Abstract
Novel 2-aminopyrimidine derivatives were prepared from acyclic starting materials, benzylidene acetones and ammonium thiocyanates, via 5 steps, including ring closure, aromatization, S-methylation, oxidation to methylsulfonyl compounds, and formation of guanidines with suitable amines. The prepared compounds differ from each other by the substitutions of their amino group and of their phenyl ring. The 2-aminopyrimidines were tested by use of microplate assays for their in vitro activities against a causative organism of sleeping sickness, Trypanosoma brucei rhodesiense, as well as against a causative organism of malaria, Plasmodium falciparum NF54. Their cytotoxic properties were determined with L-6 cells (rat skeletal myoblasts). Some of the compounds exhibited quite good antitrypanosomal activity, and others showed excellent antiplasmodial activity. The influence of the structural modifications on these activities is discussed.Graphic abstract
Highlights
In the past two decades, over two billion of the world’s poorest people have been affected by neglected tropical diseases (NTDs)
human African trypanosomiasis (HAT) or sleeping sickness is caused by protozoa of the genus Trypanosoma like Trypanosoma brucei gambiense (Tbg) and Trypanosoma brucei rhodesiense (Tbr)
Partial structures of chloroquine were used as substituents for compounds 9 and 10
Summary
In the past two decades, over two billion of the world’s poorest people have been affected by neglected tropical diseases (NTDs). 4‐(4‐Methoxyphenyl)‐6‐methyl‐2‐(pyrrolidin‐1‐yl)pyrimidine (7d, C16H19N3O) Reaction of 300 mg of 5d (1.08 mmol) in 10 cm3 of dry THF with 460 mg of pyrrolidine (6.47 mmol) yielded an oil which was purified by means of CC with cyclohexane:ethyl acetate (1:1) as eluent giving 276 mg of 7d (95%).
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